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5-Iodo-7-methyl-3-methyl-sulfinyl-2-phenyl-1-benzofuran.

ABSTRACT: The title compound, C(16)H(13)IO(2)S, was prepared by the oxidation of 5-iodo-7-methyl-3-methyl-sulfanyl-2-phenyl-1-benzofuran with 3-chloro-peroxy-benzoic acid. The phenyl ring makes a dihedral angle of 27.17?(9)° with the plane of the benzofuran fragment, with the O atom and the methyl group of the methyl-sulfinyl substituent lying on opposite sides of this plane. The crystal structure exhibits inter-molecular C-H?I inter-actions, and an I?O halogen bond of 3.107?(2)?Å with a nearly linear C-I?O angle of 173.73?(6)°.

SUBMITTER: Choi HD

PROVIDER: S-EPMC2961360 | biostudies-literature | 2008 May

REPOSITORIES: biostudies-literature

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5-Iodo-7-methyl-3-methyl-sulfinyl-2-phenyl-1-benzofuran.

Choi Hong Dae HD Seo Pil Ja PJ Kim Byung Ki BK Son Byeng Wha BW Lee Uk U

Acta crystallographica. Section E, Structure reports online 20080521 Pt 6

The title compound, C(16)H(13)IO(2)S, was prepared by the oxidation of 5-iodo-7-methyl-3-methyl-sulfanyl-2-phenyl-1-benzofuran with 3-chloro-peroxy-benzoic acid. The phenyl ring makes a dihedral angle of 27.17 (9)° with the plane of the benzofuran fragment, with the O atom and the methyl group of the methyl-sulfinyl substituent lying on opposite sides of this plane. The crystal structure exhibits inter-molecular C-H⋯I inter-actions, and an I⋯O halogen bond of 3.107 (2) Å with a nearly linear C-I ...[more]

PMID: 21202627

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5-Iodo-2-phenyl-3-phenyl-sulfinyl-1-benzofuran.

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5-Iodo-2,7-dimethyl-3-phenyl-sulfinyl-1-benzofuran.

Project description:The title compound, C(16)H(13)IO(2)S, was prepared by the oxidation of 5-iodo-2,7-dimethyl-3-phenyl-sulfanyl-1-benzofuran using 3-chloro-perbenzoic acid. The O atom and the phenyl group of the phenyl-sulfinyl substituent lie on opposite sides of the plane of the benzofuran system. The phenyl ring is nearly perpendicular to the plane of the benzofuran fragment [89.15 (5)°]. The crystal structure is stabilized by an I⋯O halogen bond [I⋯O = 3.177 (2) Å and C-I⋯O = 175.68 (6)°] linking mol-ecules into centrosymmetric dimers and by a weak C-H⋯π inter-action between a phenyl H atom and the furan ring of the benzofuran system.

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Project description:The title compound, C(15)H(12)O(2)S, was prepared by the oxidation of 3-methyl-sulfanyl-2-phenyl-1-benzofuran with 3-chloro-peroxy-benzoic acid. The phenyl ring makes a dihedral angle of 37.65?(8)° with the plane of the benzofuran fragment. The O atom and the methyl group of the methyl-sulfinyl substituent lie on opposite sides of the plane of the benzofuran ring system. The crystal structure is stabilized by aromatic ?-? inter-actions between the benzene rings of neighbouring mol-ecules [centroid-centroid distance = 3.549?(2)?Å] and by inter-molecular C-H?O inter-actions.

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2-Methyl-3-phenyl-sulfinyl-1-benzofuran.

Project description:The title compound, C(15)H(12)O(2)S, was prepared by the oxidation of 2-methyl-3-phenyl-sulfanyl-1-benzofuran with 3-chloro-peroxy-benzoic acid. The O atom and the phenyl group of the phenyl-sulfinyl substituent lie on opposite sides of the plane of the benzofuran system. The phenyl ring makes a dihedral angle of 78.76 (4)° with the benzofuran mean plane. The crystal structure is stabilized by π-π inter-actions between the furan and benzene rings of neighbouring mol-ecules [centroid-centroid distance = 4.017 (3) Å]. In addition, the crystal structure exhibits inter-molecular C-H⋯π and C-H⋯O inter-actions.

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2-(4-Iodo-phen-yl)-5-methyl-3-methyl-sulfinyl-1-benzofuran.

Project description:The title compound, C(16)H(13)IO(2)S, was prepared by the oxidation of 2-(4-iodo-phen-yl)-5-methyl-3-methyl-sulfanyl-1-benzofuran with 3-chloro-peroxy-benzoic acid. The 4-iodo-phenyl ring makes a dihedral angle of 37.97 (9)° with the plane of the benzofuran fragment, and the O atom and the methyl group of the methyl-sulfinyl substituent lie on opposite sides of this plane. The mol-ecular packing is stabilized by C-H⋯π inter-actions between H atoms on the 4-iodo-phenyl ring and the benzofuran rings, and by an I⋯O halogen bond of 3.252 (2) Å with a nearly linear C-I⋯O angle of 163.06 (8)°. In addition, the stacked mol-ecules exhibit inversion-related S⋯O contacts [3.209 (2) Å] involving the sulfinyl groups.

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2,4,5,6-Tetra-methyl-3-phenyl-sulfinyl-1-benzofuran.

Project description:In the title compound, C(18)H(18)O(2)S, the phenyl ring makes a dihedral angle of 87.47?(6)° with the mean plane of the benzofuran fragment. In the crystal, mol-ecules are linked by weak inter-molecular C-H?O hydrogen bonds and C-H?? inter-actions.

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2,4,6,7-Tetra-methyl-3-phenyl-sulfinyl-1-benzofuran.

Project description:In the title compound, C(18)H(18)O(2)S, the O atom and the phenyl group of the phenyl-sulfinyl substituent lie on opposite sides of the planar benzofuran fragment. The phenyl ring is nearly perpendicular to the benzofuran system [88.56 (7)°] and is tilted slightly towards it. Molecules form pseudo-helices along the a axis. The crystal structure is stabilized by a C-H⋯π inter-action between a methyl H atom and the phenyl ring of the phenyl-sulfinyl substituent, and by intra- and inter-molecular C-H⋯O inter-actions.

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Methyl 2-(5-iodo-7-methyl-3-methyl-sulfinyl-1-benzofuran-2-yl)acetate.

Project description:There are two symmetry-independent mol-ecules in the asymmetric unit of the title compound, C(13)H(13)IO(4)S. In each mol-ecule, the O atom and the methyl group of the methyl-sulfinyl substituent lie on opposite sides of the plane of the benzofuran fragment. The crystal structure is stabilized by aromatic π-π inter-actions between the benzene and furan ring [centroid-centroid distance = 3.866 (7) Å], and by inter-molecular C-H⋯π inter-actions and a sulfin-yl-sulfinyl inter-action [S⋯O = 3.025 (4) Å]. The crystal structure also exhibits weak inter-molecular C-H⋯O hydrogen bonds and two different I⋯O halogen bonds.

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2-(4-Fluoro-phen-yl)-5-iodo-3-phenyl-sulfinyl-1-benzofuran.

Project description:In the title compound, C(20)H(12)FIO(2)S, the dihedral angles between the mean plane [r.m.s. deviation = 0.014?(1)?Å] of the benzofuran fragment and the pendant 4-fluoro-phenyl and phenyl rings are 8.0?(1) and 86.06?(6)°, respectively. In the crystal, mol-ecules are linked by weak C-H?O hydrogen bonds. The crystal structure also exhibits weak ?-? inter-actions between the furan and benzene rings of neighbouring mol-ecules [centroid-centroid distance = 3.547?(2)?Å, inter-planar distance = 3.397?(2)?Å and slippage = 1.021?(2)?Å].

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